Retirement Roundtable
At Cypress Financial Group, we are committed to helping you pursue your long-term financial goals. As specialists in retirement planning and estate conservation, our podcast helps address the concerns you may have about your financial future, such as Will I be able to retire early? How much money will I need to retire? How can I get the most out of my 401(k)? Should I have a traditional IRA or a Roth IRA? How can I best position my investments? What kind of insurance might I need? How can my children get the most out of my estate? What do I need to know about wills, trusts, and probate? Learn more about our practice: https://cypressfinancial.net/about/
Episodes
Is DIY retirement planning putting your future at risk? This episode explores the pitfalls of going it alone, the realities of annuities and CDs, and why liquidity matters for financial security. Host John Scallan breaks down how market changes, surrender charges, and tax strategies can impact your nest egg. Learn why a second opinion and understanding tax deferral could make all the difference in building a stress-free retirement.
...Are you afraid to spend your own retirement savings? Nearly half of American retirees suffer from “spendophobia”—the fear of using the money they worked so hard to save. This episode with John Scallan explores why making the leap from saving to spending is so difficult, how simple mistakes can leave your financial future exposed, and why understanding your risk and having a clear plan is essential. Hear real stori...
What happens when your retirement timeline is suddenly rewritten by a layoff? This episode with John Scallan tackles the emotional and financial impact of unexpected job loss near retirement, offering practical strategies for bridging income gaps, managing healthcare costs, and making smart moves with RMDs and Roth conversions. Discover how to build a resilient plan and redefine your next chapter with confidence.
This episode with John Scallan explores the realities of required minimum distributions (RMDs), the pros and cons of lump sum versus monthly withdrawals, and why annuities are making a comeback as a source of guaranteed income. Discover how staying engaged with your finances and building a plan for the distribution phase can help you navigate retirement with confidence—without winging it or relying on outdated advice.
Are hidden “termites” quietly eating away at your retirement savings? This episode of the Retirement Roundtable exposes the fees you don’t see, the dangers of overlapping investments, and why a second opinion could be your best financial move. John Scallan explains how debt, diversification, and advisor red flags can make or break your retirement plan. Learn how to spot costly mistakes, understand what you really ...
What do Halloween and retirement have in common? More than you think. This episode uses spooky season as a lens to explore the biggest fears in retirement—running out of money, declining health, and boredom—and how preparation, adaptability, and honest conversations can help you face them head-on. Hear personal stories and practical advice from John Scallan on building a retirement plan that’s ready for life&rsquo...
What happens when a market “melt-up” collides with the fear of running out of money in retirement? This episode with John Scallan explores the emotional and financial challenges facing retirees, from sudden income gaps to the struggle of spending hard-earned savings. Discover why timing matters, how part-time work can reshape your future, and practical steps to stay resilient when uncertainty strikes.
What happens when your retirement dreams collide with reality—and even a lottery win isn’t enough? In this episode, John Scallan explores the financial anxieties of Gen X, the pitfalls of windfall income, and why retirement planning is more complex than ever. Hear real stories, expert advice, and practical steps for building income streams, managing debt, and making smart choices—whether you’re facing a wind...
What if your retirement dreams were derailed by a triple whammy of falling interest rates, rising healthcare costs, and unexpected taxes? This episode explores how shifting rates impact savings, why the “magic number” for retirement is different for everyone, and how tax surprises can upend your plans. John Scallan breaks down strategies for building income streams, managing risk, and staying ahead of financial curvebal...
Could you really live to 100—and if so, are you ready for it? This episode explores the three essential questions every retiree must ask: Can I afford a longer life? Who will I share it with? And how will I find purpose in my golden years? Join John Scallan as he breaks down the strategies, stories, and real-life lessons for thriving in a century-long retirement.
For more information, please visit www.CypressFinancial.net!
What happens when retirement planning collides with the complexities of “grey divorce” and legacy concerns? This episode with John Scallan dives into real-life stories, including a surprising call from an ex-spouse worried about a seven-figure 401(k), and explores how couples—and families—navigate risk, income, and communication in retirement. Discover strategies for aligning financial goals, managing debt, ...
What if winning the lottery or retiring early isn’t the answer you think it is? This episode with John Scallan explores the realities behind sudden wealth, risk tolerance, and the difference between financial advice and self-management. Discover why purpose matters as much as money, and how asking the right questions can shape your retirement journey.
For more information, please visit www.CypressFinancial.net!
What’s more uncomfortable—talking about family finances or losing half your inheritance to taxes? In this episode, John Scallan tackles the largest wealth transfer in U.S. history, the truth about Social Security taxes, and why 2025 may be your golden window for Roth conversions. With practical advice on initiating tough family conversations and maximizing tax strategies, this episode is a must-listen for anyone plannin...
What if your retirement plan got less attention than your vacation itinerary? In this episode, John Scallan challenges listeners to rethink their financial priorities, offering insights on bond risks, Social Security uncertainty, and the value of a second opinion. From short-term bond strategies to advisor red flags, the conversation is packed with practical advice for building a flexible, responsive retirement plan. Whether you're...
What if living too long became your biggest financial fear? In this episode of the Retirement Roundtable, John Scallan breaks down three powerful tools to turn your savings into lifetime income—no matter how long you live. From MIGAs to FIAs with income riders, learn how to build your own pension and protect against market downturns while keeping liquidity for emergencies. Whether you're nearing retirement or already there, t...
What if one dollar could cost you thousands in retirement? In this episode of Retirement Roundtable, John Scallan tackles the emotional side of financial planning and the real risks retirees face—from Social Security cuts to the hidden Medicare surcharge known as IRMAA. He breaks down urgent tax-saving opportunities for those aged 60–63 and explains why planning five years ahead can make all the difference. If you'...
Think you’ve got time to plan for retirement? Think again. In this episode, John Scallan breaks down how procrastination, hidden 401(k) fees, and misunderstood annuities can quietly sabotage your financial future. From time optimists to costly investment missteps, learn why waiting could cost you thousands—and how to take action now. Whether you're just starting or already retired, this conversation offers practical str...
What if outdated fears are keeping you from the best retirement tools available today? In this episode, John Scallan breaks down the evolution of annuities, the role of index funds, and why guaranteed income is more critical than ever. From the “golden age of annuities” to dynamic income strategies that span 30+ years, this conversation is packed with practical insights for anyone approaching retirement. Plus, a candid ...
Can timing the market really beat a smart plan? In this episode, John Scallan breaks down why chasing perfect moments can cost you—and how strategic models can protect your retirement. From Roth conversions to hidden costs like healthcare and family emergencies, John shares actionable insights to help you preserve assets and build income. Plus, hear thoughts on financial expert Ed Slott, inheritance strategies, and why retire...
What if your biggest retirement mistake was trying to time the market? In this episode, John Scallan of Cypress Financial breaks down why emotional investing can cost you—and how strategic planning can save you. From Roth IRA conversions and inherited wealth to hidden retirement costs like healthcare and taxes, John shares practical advice for building income that lasts. Plus, a reminder that retirement plans, like gardens, n...
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